CA2521736C - Curable organopolysiloxane resin composition for optical waveguides, optical waveguide, and fabrication process thereof - Google Patents
Curable organopolysiloxane resin composition for optical waveguides, optical waveguide, and fabrication process thereof Download PDFInfo
- Publication number
- CA2521736C CA2521736C CA2521736A CA2521736A CA2521736C CA 2521736 C CA2521736 C CA 2521736C CA 2521736 A CA2521736 A CA 2521736A CA 2521736 A CA2521736 A CA 2521736A CA 2521736 C CA2521736 C CA 2521736C
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- Canada
- Prior art keywords
- component
- cured
- cured product
- organopolysiloxane resin
- hydrocarbon groups
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 230000003287 optical effect Effects 0.000 title claims abstract description 199
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 141
- 239000011342 resin composition Substances 0.000 title claims abstract description 57
- 238000000034 method Methods 0.000 title claims abstract description 41
- 230000008569 process Effects 0.000 title claims abstract description 39
- 238000004519 manufacturing process Methods 0.000 title description 19
- 229920005989 resin Polymers 0.000 claims abstract description 99
- 239000011347 resin Substances 0.000 claims abstract description 99
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 46
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 34
- 125000005375 organosiloxane group Chemical group 0.000 claims abstract description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 21
- 150000003961 organosilicon compounds Chemical class 0.000 claims abstract description 15
- 238000006459 hydrosilylation reaction Methods 0.000 claims abstract description 14
- 239000003085 diluting agent Substances 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims description 89
- 238000010438 heat treatment Methods 0.000 claims description 66
- 238000005253 cladding Methods 0.000 claims description 51
- 239000000758 substrate Substances 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 238000000465 moulding Methods 0.000 claims description 10
- 229910020485 SiO4/2 Inorganic materials 0.000 claims description 9
- 230000001105 regulatory effect Effects 0.000 claims description 5
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 claims 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 238000004891 communication Methods 0.000 abstract description 13
- 239000002904 solvent Substances 0.000 abstract description 11
- 230000005540 biological transmission Effects 0.000 abstract description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
- 239000011162 core material Substances 0.000 description 42
- 238000001723 curing Methods 0.000 description 28
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
- 150000002430 hydrocarbons Chemical group 0.000 description 23
- 239000000463 material Substances 0.000 description 20
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 16
- 238000009833 condensation Methods 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- 238000000576 coating method Methods 0.000 description 14
- 239000010410 layer Substances 0.000 description 14
- 239000010408 film Substances 0.000 description 13
- 230000003301 hydrolyzing effect Effects 0.000 description 13
- 239000011248 coating agent Substances 0.000 description 12
- 230000005494 condensation Effects 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 238000013019 agitation Methods 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 10
- 230000007423 decrease Effects 0.000 description 10
- 230000003472 neutralizing effect Effects 0.000 description 10
- 125000005372 silanol group Chemical group 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000005266 casting Methods 0.000 description 9
- 238000004528 spin coating Methods 0.000 description 9
- 230000018044 dehydration Effects 0.000 description 8
- 238000006297 dehydration reaction Methods 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 229910052697 platinum Inorganic materials 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 239000012792 core layer Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 230000010287 polarization Effects 0.000 description 7
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 229910000077 silane Inorganic materials 0.000 description 6
- 239000003377 acid catalyst Substances 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 238000005336 cracking Methods 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000002834 transmittance Methods 0.000 description 5
- 230000004580 weight loss Effects 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 150000001367 organochlorosilanes Chemical class 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229920002379 silicone rubber Polymers 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 238000005452 bending Methods 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- SOCDYVOHMCDZND-UHFFFAOYSA-N ethenyl-hydroxy-methyl-phenylsilane Chemical class C=C[Si](O)(C)C1=CC=CC=C1 SOCDYVOHMCDZND-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000001282 organosilanes Chemical class 0.000 description 3
- 229920003217 poly(methylsilsesquioxane) Polymers 0.000 description 3
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000004945 silicone rubber Substances 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 3
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- 229910020487 SiO3/2 Inorganic materials 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000005054 phenyltrichlorosilane Substances 0.000 description 2
- 238000000206 photolithography Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 2
- 125000005023 xylyl group Chemical group 0.000 description 2
- KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 1
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- NECRQCBKTGZNMH-UHFFFAOYSA-N 3,5-dimethylhex-1-yn-3-ol Chemical compound CC(C)CC(C)(O)C#C NECRQCBKTGZNMH-UHFFFAOYSA-N 0.000 description 1
- GRGVQLWQXHFRHO-UHFFFAOYSA-N 3-methylpent-3-en-1-yne Chemical compound CC=C(C)C#C GRGVQLWQXHFRHO-UHFFFAOYSA-N 0.000 description 1
- MQSZOZMNAJHVML-UHFFFAOYSA-N 3-phenylbut-1-yn-1-ol Chemical compound OC#CC(C)C1=CC=CC=C1 MQSZOZMNAJHVML-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000233803 Nypa Species 0.000 description 1
- 235000005305 Nypa fruticans Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- FALOWFFVOUBGKZ-UHFFFAOYSA-N [bis(ethenyl)-methylsilyl]oxy-diphenyl-trimethylsilyloxysilane Chemical compound C=1C=CC=CC=1[Si](O[Si](C)(C=C)C=C)(O[Si](C)(C)C)C1=CC=CC=C1 FALOWFFVOUBGKZ-UHFFFAOYSA-N 0.000 description 1
- YKSADNUOSVJOAS-UHFFFAOYSA-N [bis[(dimethyl-$l^{3}-silanyl)oxy]-phenylsilyl]oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](O[Si](C)C)(O[Si](C)C)C1=CC=CC=C1 YKSADNUOSVJOAS-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- XSDCTSITJJJDPY-UHFFFAOYSA-N chloro-ethenyl-dimethylsilane Chemical compound C[Si](C)(Cl)C=C XSDCTSITJJJDPY-UHFFFAOYSA-N 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 description 1
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- VDCSGNNYCFPWFK-UHFFFAOYSA-N diphenylsilane Chemical compound C=1C=CC=CC=1[SiH2]C1=CC=CC=C1 VDCSGNNYCFPWFK-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001312 dry etching Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- KPWVUBSQUODFPP-UHFFFAOYSA-N ethenyl-(ethenyl-methyl-phenylsilyl)oxy-methyl-phenylsilane Chemical compound C=1C=CC=CC=1[Si](C)(C=C)O[Si](C)(C=C)C1=CC=CC=C1 KPWVUBSQUODFPP-UHFFFAOYSA-N 0.000 description 1
- BITPLIXHRASDQB-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)C=C BITPLIXHRASDQB-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000005048 methyldichlorosilane Substances 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- PKELYQZIUROQSI-UHFFFAOYSA-N phosphane;platinum Chemical class P.[Pt] PKELYQZIUROQSI-UHFFFAOYSA-N 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 238000001020 plasma etching Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 1
- 229920000734 polysilsesquioxane polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000807 solvent casting Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- CLDZUYIZPFQYFS-UHFFFAOYSA-N tetrakis[methyl(phenyl)silyl] silicate Chemical compound C=1C=CC=CC=1[SiH](C)O[Si](O[SiH](C)C=1C=CC=CC=1)(O[SiH](C)C=1C=CC=CC=1)O[SiH](C)C1=CC=CC=C1 CLDZUYIZPFQYFS-UHFFFAOYSA-N 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- BRIBPRDKSMBVRH-UHFFFAOYSA-N tris[[methyl(phenyl)silyl]oxy]silane Chemical compound C[SiH](O[SiH](O[SiH](C)c1ccccc1)O[SiH](C)c1ccccc1)c1ccccc1 BRIBPRDKSMBVRH-UHFFFAOYSA-N 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C39/00—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor
- B29C39/003—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor characterised by the choice of material
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
- G02B6/10—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type
- G02B6/12—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type of the integrated circuit kind
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/70—Siloxanes defined by use of the MDTQ nomenclature
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/02—Flame or fire retardant/resistant
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/10—Transparent films; Clear coatings; Transparent materials
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
- G02B6/10—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type
- G02B6/12—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type of the integrated circuit kind
- G02B2006/12035—Materials
- G02B2006/12061—Silicon
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
- G02B6/10—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type
- G02B6/12—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type of the integrated circuit kind
- G02B2006/12035—Materials
- G02B2006/12069—Organic material
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Optical Integrated Circuits (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Silicon Polymers (AREA)
- Optical Fibers, Optical Fiber Cores, And Optical Fiber Bundles (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003103252 | 2003-04-07 | ||
| JP2003-103252 | 2003-04-07 | ||
| JP2003-160302 | 2003-06-05 | ||
| JP2003160302A JP2004361692A (ja) | 2003-04-07 | 2003-06-05 | 光伝送部材用硬化性オルガノポリシロキサン樹脂組成物、オルガノポリシロキサン樹脂硬化物からなる光伝送部材および光伝送部材の製造方法 |
| PCT/JP2004/005014 WO2004090041A2 (en) | 2003-04-07 | 2004-04-07 | Curable organopolysiloxane resin composition for optical transmission components, optical transmission components, and fabrication process thereof |
Publications (2)
| Publication Number | Publication Date |
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| CA2521736A1 CA2521736A1 (en) | 2004-10-21 |
| CA2521736C true CA2521736C (en) | 2013-07-02 |
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| CA2521736A Expired - Fee Related CA2521736C (en) | 2003-04-07 | 2004-04-07 | Curable organopolysiloxane resin composition for optical waveguides, optical waveguide, and fabrication process thereof |
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| US7509011B2 (en) * | 2004-01-15 | 2009-03-24 | Poa Sana Liquidating Trust | Hybrid waveguide |
| EP1749860A4 (en) * | 2004-05-14 | 2009-12-23 | Dow Corning Toray Co Ltd | FREE FILMS MANUFACTURED FROM ORGANOPOLYSILOXANE RESINS, THEIR PRODUCTION PROCESS AND LAMINATED FILMS |
| US7676131B2 (en) * | 2004-06-04 | 2010-03-09 | Poa Sana Liquidating Trust | Waveguide with a three-dimensional lens |
| US7471865B2 (en) * | 2004-06-04 | 2008-12-30 | Poa Sana Liquidating Trust | Apparatus and method for a molded waveguide for use with touch screen displays |
| JP4647941B2 (ja) * | 2004-06-23 | 2011-03-09 | 東レ・ダウコーニング株式会社 | シリコーンレジンとシリコーンゴムの一体化成形体、その製造方法および硬化性シリコーンレジン組成物 |
| US7496266B2 (en) * | 2004-06-25 | 2009-02-24 | Omron Corporation | Film waveguide, method of manufacturing film waveguide, and electronic device |
| KR100860657B1 (ko) * | 2004-06-25 | 2008-09-26 | 오므론 가부시키가이샤 | 필름 광 도파로 및 그 제조 방법 및 전자 기기 장치 |
| JP4593348B2 (ja) * | 2005-04-20 | 2010-12-08 | 日本ペイント株式会社 | ポリシラン組成物並びに光導波路及びその製造方法 |
| JP4636242B2 (ja) * | 2005-04-21 | 2011-02-23 | 信越化学工業株式会社 | 光半導体素子封止材及び光半導体素子 |
| AU2011235989B2 (en) * | 2005-06-10 | 2013-08-01 | Accenture Global Services Limited | Electronic vehicle identification |
| US20090130463A1 (en) * | 2005-10-05 | 2009-05-21 | John Dean Albaugh | Coated Substrates and Methods for their Preparation |
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| US20080031584A1 (en) * | 2006-08-02 | 2008-02-07 | National Semiconductor Corporation | Apparatus and method for a singulation of polymer waveguides using photolithography |
| JP2010508377A (ja) * | 2006-08-28 | 2010-03-18 | ダウ・コーニング・コーポレイション | 光学部品およびシリコーン組成物および光学部品の成型方法 |
| EP2095446A1 (en) * | 2006-12-20 | 2009-09-02 | Dow Corning Corporation | Composite article including a cation-sensitive layer |
| JP4605402B2 (ja) * | 2007-05-25 | 2011-01-05 | 信越化学工業株式会社 | 光導波板用液状シリコーンゴム組成物 |
| CN101681010A (zh) * | 2007-07-03 | 2010-03-24 | 柯尼卡美能达精密光学株式会社 | 摄影装置的制造方法、摄影装置以及光学元件 |
| CN101910255B (zh) | 2008-01-08 | 2013-07-10 | 道康宁东丽株式会社 | 倍半硅氧烷树脂 |
| US9023433B2 (en) * | 2008-01-15 | 2015-05-05 | Dow Corning Corporation | Silsesquioxane resins and method of using them to form an antireflective coating |
| WO2009111122A2 (en) * | 2008-03-04 | 2009-09-11 | Dow Corning Corporation | Silsesquioxane resins |
| EP2265666B1 (en) * | 2008-03-04 | 2015-03-25 | Dow Corning Corporation | Silicone composition, silicone adhesive, coated and laminated substrates |
| JP5581224B2 (ja) * | 2008-03-05 | 2014-08-27 | ダウ・コーニング・コーポレイション | シルセスキオキサン樹脂 |
| US8809482B2 (en) | 2008-12-10 | 2014-08-19 | Dow Corning Corporation | Silsesquioxane resins |
| WO2010068337A1 (en) * | 2008-12-10 | 2010-06-17 | Dow Corning Corporation | Wet-etchable antireflective coatings |
| US9080077B2 (en) | 2009-12-21 | 2015-07-14 | Dow Corning Corporation | Methods for fabricating flexible waveguides using alkyl-functional silsesquioxane resins |
| CN101819296B (zh) * | 2010-03-05 | 2011-12-28 | 中国人民解放军国防科学技术大学 | 一种用于光互连的聚硅氧烷光波导的制备方法 |
| US8742009B2 (en) | 2010-06-04 | 2014-06-03 | Shin-Etsu Chemical Co., Ltd. | Temporary adhesive composition, and method of producing thin wafer |
| JP5170471B2 (ja) * | 2010-09-02 | 2013-03-27 | 信越化学工業株式会社 | 低ガス透過性シリコーン樹脂組成物及び光半導体装置 |
| JP2012074512A (ja) * | 2010-09-28 | 2012-04-12 | Sekisui Chem Co Ltd | 光半導体装置用ダイボンド材及びそれを用いた光半導体装置 |
| US20130256741A1 (en) * | 2010-12-08 | 2013-10-03 | Brian R. Harkness | Siloxane Compositions Suitable For Forming Encapsulants |
| KR20130126946A (ko) * | 2010-12-08 | 2013-11-21 | 다우 코닝 코포레이션 | 봉지재의 형성에 적합한 이산화티타늄 나노입자 함유 실록산 조성물 |
| JP5592330B2 (ja) * | 2011-10-07 | 2014-09-17 | 信越化学工業株式会社 | 仮接着剤組成物、及びそれを用いた薄型ウエハの製造方法 |
| JP6084808B2 (ja) * | 2012-10-24 | 2017-02-22 | 東レ・ダウコーニング株式会社 | オルガノポリシロキサン、硬化性シリコーン組成物、その硬化物、および光半導体装置 |
| JP6157085B2 (ja) | 2012-10-24 | 2017-07-05 | 東レ・ダウコーニング株式会社 | 硬化性シリコーン組成物、その硬化物、および光半導体装置 |
| JP6081774B2 (ja) * | 2012-10-30 | 2017-02-15 | 東レ・ダウコーニング株式会社 | 硬化性シリコーン組成物、その硬化物、および光半導体装置 |
| WO2014164449A1 (en) * | 2013-03-13 | 2014-10-09 | Applied Materials, Inc. | Multi-zone heated esc with independent edge zones |
| US9909007B2 (en) * | 2013-08-29 | 2018-03-06 | Dow Corning Corporation | Curable silicone composition, cured product thereof, and optical semiconductor device |
| TWI648345B (zh) * | 2013-12-16 | 2019-01-21 | 道康寧公司 | 選擇性遮光之光物理材料及包括此等選擇性遮光之光物理材料的光學裝置 |
| JPWO2018235200A1 (ja) * | 2017-06-21 | 2019-06-27 | 三菱電機株式会社 | 光導波路、光回路および半導体レーザ |
| WO2020086675A1 (en) * | 2018-10-23 | 2020-04-30 | Sigma International | Lighted device useful in a vehicle interior |
| US11886001B2 (en) * | 2019-12-20 | 2024-01-30 | Snap Inc. | Optical waveguide fabrication process |
| JP7696089B2 (ja) * | 2021-09-24 | 2025-06-20 | パナソニックＩｐマネジメント株式会社 | 光導波路用材料 |
| TW202334318A (zh) * | 2022-02-24 | 2023-09-01 | 美商陶氏有機矽公司 | 可固化聚矽氧組成物 |
| JP2025507537A (ja) * | 2022-02-24 | 2025-03-21 | ダウ シリコーンズ コーポレーション | 硬化性シリコーン組成物及びその硬化物 |
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| US3948848A (en) * | 1975-08-04 | 1976-04-06 | Dow Corning Corporation | Low temperature solventless silicone resins |
| US4198131A (en) * | 1978-03-23 | 1980-04-15 | Dow Corning Corporation | Silicone resin optical devices |
| US4529789A (en) * | 1984-03-23 | 1985-07-16 | Dow Corning Corporation | Liquid curable polyorganosiloxane compositions |
| CA1230192A (en) | 1984-03-23 | 1987-12-08 | Loretta A. Kroupa | Liquid curable polyorganosiloxane compositions |
| JPS61275706A (ja) * | 1985-05-30 | 1986-12-05 | Sumitomo Electric Ind Ltd | 光導波路 |
| US4830461A (en) * | 1987-01-29 | 1989-05-16 | Bridgestone Corporation | Pressure-sensitive sensors |
| JP2726043B2 (ja) | 1987-03-06 | 1998-03-11 | 株式会社ブリヂストン | 可撓性光導波路 |
| JPH01143605A (ja) | 1987-11-30 | 1989-06-06 | Kagawa Atsuko | 多孔質フィルムの製造方法 |
| JPH04214730A (ja) * | 1990-12-13 | 1992-08-05 | Shin Etsu Chem Co Ltd | オルガノポリシロキサンの製造方法 |
| JPH07306301A (ja) * | 1994-05-13 | 1995-11-21 | Dow Corning Kk | 光学素子及びその製造方法 |
| JPH08176444A (ja) * | 1994-10-26 | 1996-07-09 | Nippon Telegr & Teleph Corp <Ntt> | 高分子光学材料及びこれを用いた光導波路 |
| JP3449456B2 (ja) * | 1997-02-05 | 2003-09-22 | 信越化学工業株式会社 | オルガノポリシロキサン樹脂組成物 |
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- 2004-04-07 EP EP04726300A patent/EP1611203B1/en not_active Expired - Lifetime
- 2004-04-07 US US10/552,191 patent/US20070025678A1/en not_active Abandoned
- 2004-04-07 WO PCT/JP2004/005014 patent/WO2004090041A2/en active Application Filing
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2005
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| Publication number | Publication date |
|---|---|
| EP1611203B1 (en) | 2011-04-06 |
| WO2004090041A2 (en) | 2004-10-21 |
| KR101092249B1 (ko) | 2011-12-12 |
| CA2521736A1 (en) | 2004-10-21 |
| KR20060030465A (ko) | 2006-04-10 |
| US20070025678A1 (en) | 2007-02-01 |
| WO2004090041A3 (en) | 2005-01-27 |
| ATE504634T1 (de) | 2011-04-15 |
| JP2004361692A (ja) | 2004-12-24 |
| EP1611203A2 (en) | 2006-01-04 |
| DE602004032121D1 (de) | 2011-05-19 |
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